Guess Why Jerry's Relationships With These Women Imploded On Seinfeld

When someone mentions Seinfeld, several things happen at once inside the mind. Funky bass riffs start bouncing around the cranium, with Kramer’s rapid apartment entrances serving as percussion, and then a flipbook of female faces passes by of all the failed relationships that Jerry has had throughout the show’s nine seasons. And if you’re me, it’s all capped off with Jerry saying the line, “He’s my butler.”

With Seinfeld hitting Hulu recently as part of a giant deal, fans are no longer tethered to catching the show’s (admittedly endless) repeats on TV, and can watch whatever episode they want, whenever they want. And we thought it would be fun to test everyone’s memory of the series by offering up an image of one of Jerry’s many girlfriends and getting you guys to guess the reason why it never worked out between them. No points awarded if your answer is “because it never works out with Jerry.” Let’s kick things off with an easy one.

ROUND ONE

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Name: Sidra (Teri Hatcher)

Season: 4

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The Reason: Despite being extremely attracted to her, Jerry initially breaks it off with Sidra in “The Implant” after Elaine convinces him that her breasts are fake, and his attempt to rekindle their romance (following Elaine getting hands-on proof that they’re real) is thwarted after Sidra realizes Jerry and Elaine are friends. Final verdict? They’re real, and they’re spectacular.

ROUND TWO

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Name: Amy (Anna Gunn)

Season: 5

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The Reason: Using his supposedly excellent eyesight – which is later proven to be horrible – George thinks he sees Amy kissing Jerry’s cousin Jeffrey in “The Glasses,” and things get uncomfortable after Jerry wrongfully accuses her. It’s temporarily smooth sailing once it’s clear that George can’t see shit, but a later misunderstanding involving Jeffrey and a pair of Paul Simon tickets seals the deal for Jerry and Amy’s breakup.

ROUND THREE

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Name: Cindy (Angela Featherstone)

Season: 9

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The Reason: Cindy and Jerry first got together after he hired her as his maid in “The Maid.” But it doesn’t take her long to cut that whole housekeeping thing out of the equation, even though he’s still paying her and they’re still having sex. This makes him feel like his money is only going towards the lovemaking, and when he brings that up, everything goes south. It doesn’t help that he tries giving her last paycheck to her while he’s in his car and she’s walking around on the street in “eveningwear,” which a cop catches him doing.

ROUND FOUR

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Name: Sandra (Lisa Malkiewicz)

Season: 4

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The Reason: In a round of dirty-talking at Jerry’s apartment – which is apparently heated enough to get George to squirt his ketchup all over Monk’s floor – Sandra starts talking about panties, and Jerry’s impulsive response is “You mean the panties your mother laid out for you?” It might not be the worst response to sex talk in human history, but it was certainly abnormal enough to get Sandra to pull anchor and end their sesh in “The Cheever Letters.”

ROUND FIVE

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Name: Margaret (Marita Gerahty)

Season: 6

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The Reason: We know that Jerry has very little patience and acceptance for many things, and Newman probably sits at the top of that list. So when Jerry finds out in “The Big Salad” that Margaret used to date Newman, and that Newman, not Margaret, was the one who put an end to their relationship, the mental anguish is absolutely too much for Jerry to bear. I mean, she was so clearly out of his league, right?

ROUND SIX

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Name: Jane (Jami Gertz)

Season: 5

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The Reason: Jane and her discernible voice were doomed from the start in “The Stall.” Her refusal to spare a square for Elaine in a movie theater restroom aside, Kramer recognizes her as the phone sex operator he’d been talking to who went by the name Erica. She initially denies it, but after Elaine gets her toilet paper revenge, Jane’s true (vocal) colors come out and she breaks up with Jerry, while also telling Kramer to stop calling her.

ROUND SEVEN

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Name: Christie (Lisa Deanne)

Season: 7

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The Reason: In “The Seven,” Jerry meets Christie and the two hit it off quite well, at least until Jerry starts obsessing over her wardrobe, which seems to consist of just one change of clothes. Rather than asking her about it outright – because that would be anti-Seinfeld behavior – Jerry cons his way into her apartment where he finds a suspicious picture from years previous, and gets busted while trying to search her apartment for a cache of samey outfits. She then non-surprisingly breaks up with him.

ROUND EIGHT

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Name: Celia (Julia Pennington)

Season: 9

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The Reason: One could say it was all over with as soon as Jerry saw that Celia had a giant toy collection in her apartment’s living room, complete with a G.I. Joe with the full Frogman suit. But then he made things extremely uncomfortable by drugging her so that he could invite George and Elaine to come over and play with everything. But the breakup didn’t actually come to an end until Kramer invited Celia to his Merv Griffin Show and clued her in on Jerry’s deviously childish actions.

ROUND NINE

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Name: Donna (Gretchen German)

Season: 2

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The Reason: It didn’t take long for Jerry to show off just how frivolous his feelings could be about women after Seinfeld started. In “The Phone Message,” his attraction to Donna ended after she laughed at a cotton Dockers commercial that Jerry thought was stupid. Not that she didn’t get aggravated with him after finding out that he told all of his friends about her liking the commercial. “Cotton Dockers” is good shorthand for someone with a bad sense of humor.

ROUND TEN

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Name: Jodi (Jennifer Coolidge)

Season: 5

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The Reason: Jodi is a masseuse in “The Masseuse,” and despite her and Jerry’s relationship being fine otherwise, she doesn’t seem to want to give him a massage, the very thing that he ends up obsessing over. So it’s really no surprise that he inevitably tries to force her into an impromptu massage, which causes her to break it off with him. She also really doesn’t like George, so it probably wouldn’t have worked anyway.

Using the honor system, head to the next page and let us know how well you did. Not that there’s anything wrong with doing badly.

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Nick Venable
Assistant Managing Editor

Nick is a Cajun Country native and an Assistant Managing Editor with a focus on TV and features. His humble origin story with CinemaBlend began all the way back in the pre-streaming era, circa 2009, as a freelancing DVD reviewer and TV recapper.  Nick leapfrogged over to the small screen to cover more and more television news and interviews, eventually taking over the section for the current era and covering topics like Yellowstone, The Walking Dead and horror. Born in Louisiana and currently living in Texas — Who Dat Nation over America’s Team all day, all night — Nick spent several years in the hospitality industry, and also worked as a 911 operator. If you ever happened to hear his music or read his comics/short stories, you have his sympathy.